Healthy generosity is giving without being depleted by the gift. An offering to another made while retaining ample resources of psychic energy, space, and content. Gifts may be tangible (money, an heirloom brooch, possessions) or intangible (attention, time, emotional availability, encouragement), but is a kind of care for others while the self remains generative.

Psychoanalyst Salman Akhtar suggests generosity is a mutually constructed phenomenon, one co-created in a relational context. What about those who mock generosity as foolishness? Recipients who use it as an excuse for demanding more or respond glibly “I’ll get the check next time,” diminishing a generous act into a mechanical exchange without acknowledging the warm heartedness of the deed.

Generosity is a trait of character where problematic tendencies abound. Akhtar lists several pathological forms, which sometimes overlap:

1. “Begrudging generosity”: a half-giving that demands being thanked repeatedly. “With people in whom the feeling of inner wealth and strength is not sufficiently established, bouts of generosity are often followed by an exaggerated need for appreciation and gratitude, and consequently, by persecutory anxieties of having been impoverished and robbed.” (82, Melanie Klein cited in Akhtar). The giver may remind the recipient of the hardships or sacrifice involved in securing the gift.

2. “Controlling generosity”: the proverbial gift with strings attached. This kind of pathological form is characterized by the need on the part of the giver to determine how the gift is used. One vivid example is the immigrant family who offers to pay for a child’s education if they attend medical school. (83) Akhtar notes, in this instance parents “confuse encouraging achievement with facilitating individuation.” Sometimes the "strings" attached may represent a mental balance sheet of debts owed in return for the gift. Controlling or coercive generosity can express itself also from the grave (posthumously) when a person’s estate is left to an heir on the condition they use it in a specified way.

3. “Unrelenting generosity”: has a pressurized or compulsive quality on the part of the giver, leaves them perpetually depleted and poorly correlates to the needs of the recipient. Often there is little understanding of the indulged party’s true needs and scant enjoyment in the act of giving for either person. This tendency may involve a rescue fantasy, financial overindulgence, or express itself in mothering offspring far into their adulthood. Such compulsive caretaking cloaks guilt, envy, and the wish to infantilize or control the other. The gift debilitates the recipient and hinders the enhancement of their wellbeing.

Akhtar notes lack of generosity may come from one’s “identification with a frustrating mother” whereas a different kind of problem results from modeling oneself after the bountiful mother or caregiver of abundance one did not have, but yearns to have had. (79) Generosity is inherent in childrearing and, while not always the case, Akhtar suggests childlessness is sometimes an expression of stinginess or the refusal to give.

On the healthy side of the spectrum there is the genuine good act of giving. What I call “attuned generosity” or adaptive giving arises when the beneficiary is in sync with the emotional needs of the receiver. This is especially relevant to parenting. Pediatrician D. W. Winnicott described a process of adaptive giving to the child by the mother in graduations—based on the extent of the child's needs and their growing independence. This kind of generosity enriches the self-sufficiency of the recipient. The gift may be nothing more than a simple gesture that recognizes and encourages, that fosters the other’s ability to depend on internalized good objects (their own good mental images of others) for developmental advancement, sustenance, and self-care.

“They might not need me; but they might. I'll let my head be just in sight; a smile as small as mine might be precisely their necessity” (poet Emily Dickinson).